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Oct 13 - Oct 14
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Oct 14 - Oct 15
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Our top choices for Fleming Key hotels

A modern hotel room with a large bed, a nightstand, a bedside table, and a bathroom visible through an open door.
A breakfast table with various food items and drinks, a pool in the background, and a tiled wall.
A reception area with a wooden herringbone wall, teal chairs, a wooden bench, and two framed sunset paintings.
A swimming pool with lounge chairs, surrounded by palm trees and greenery.

1. Almond Tree Inn Hotel - Adults Only

Almond Tree Inn Hotel - Adults Only
Old Town Key West
United States
John
CA $397
CA $447 total
includes taxes & fees
Oct 27 - Oct 28
Almond Tree Inn Hotel - Adults Only
A bottle of Marc's Reserve 12 FL. OZ. on a coaster with a metal table.
A front door with purple shutters, a small porch, and a doormat with 'The Artist House Circa 1890' text.
A pool with a lion head sculpture in the center.
A potted yellow orchid plant in a garden setting with a brick pathway, palm trees, and a white building in the background.

2. Artist House Key West

Artist House Key West
Key West Historic District
CA $298
CA $336 total
includes taxes & fees
Oct 29 - Oct 30
Artist House Key West
A tropical outdoor area with palm trees, hanging plants, and string lights.
A hotel room with a bed, a wooden floor, a seating area with a table and chairs, and a view of greenery outside.
A large, two-story building with a balcony, surrounded by dense tropical foliage.
An outdoor patio with a table and chairs, surrounded by lush greenery and string lights.

3. Douglas House - Adults Only

Douglas House - Adults Only
Old Town Key West
United States
Maricela
CA $225
CA $278 total
includes taxes & fees
Oct 15 - Oct 16
Douglas House - Adults Only
A pool area with lounge chairs and a table, surrounded by palm trees.
A patio with a white wicker lounge chair, a wooden table with a book and a potted plant, surrounded by lush tropical foliage and palm trees.
A hotel room with a large bed, a nightstand, a desk, a bathroom with a shower, and a painting of a pier over water on the wall.
A building with a neon sign that reads "Orchid Key Inn."

4. Orchid Key Inn - Adults Only

Orchid Key Inn - Adults Only
Old Town Key West
United States
ben
CA $363
CA $408 total
includes taxes & fees
Oct 27 - Oct 28
Orchid Key Inn - Adults Only
A modern hotel room with a white sofa, a zebra-patterned rug, and a large mirror above the sofa.
A spacious living room with a sofa, chairs, and a dining table. There are large windows with blinds, a door leading to a patio, and a ceiling with exposed beams.
A pool area with lounge chairs, a pool, and a building with a balcony and outdoor seating.
A narrow room with a bed, a potted plant, and a window with blinds.

5. Alexander's Guesthouse - Adult Exclusive

Alexander's Guesthouse - Adult Exclusive
Old Town Key West
United States
Nestor
CA $320
CA $419 total
includes taxes & fees
Oct 15 - Oct 16
Alexander's Guesthouse - Adult Exclusive
A garden pathway leading to a white gazebo with pink flowers, surrounded by lush greenery and a white fence.
A bar area with a counter, chairs, and a clock.
A bedroom with a large bed, a television on a dresser, and a view of the outdoors through a sliding door.
A couple walking along a poolside pathway surrounded by lush greenery.

6. The Gardens Hotel

The Gardens Hotel
Old Town Key West
United States
Gisele
CA $427
CA $480 total
includes taxes & fees
Oct 28 - Oct 29
The Gardens Hotel
A porch with a white railing, a bench, and a flag.
A living room with a sofa, a glass coffee table, a TV, and a painting on the wall.
A spacious bedroom with a large bed, a sitting area with a sofa and armchairs, and a dining area with a table and chairs.
A two-story white house with green shutters, a wooden door, and a white picket fence.

7. The Conch House Heritage Inn

The Conch House Heritage Inn
Old Town Key West
United States
John
CA $408
CA $459 total
includes taxes & fees
Oct 25 - Oct 26
The Conch House Heritage Inn
A gated entrance to Villas Key West with a brick pathway leading to the gate.
A house with a porch, a table, and a door with a number '6'.
A covered entrance with a brick pathway leading to a gated area, surrounded by lush greenery and plants.
A covered porch with wicker furniture, a large potted plant, and a sign for Villas Key West.

8. Key West Villas

Key West Villas
Old Town Key West
United States
Margaret
CA $371
CA $417 total
includes taxes & fees
Oct 15 - Oct 16
Key West Villas
A modern outdoor area with a pool, lounge chairs, and a bar area.
A modern hotel with a prominent glass facade, palm trees, and a clear sky.
An outdoor seating area with a modern fire feature, surrounded by lush greenery and palm trees.
A modern hotel room with a bed, sofa, coffee table, and artwork.

9. H2O Suites - Adults Only

H2O Suites - Adults Only
Old Town Key West
United States
Carmen
CA $498
CA $657 total
includes taxes & fees
Nov 2 - Nov 3
H2O Suites - Adults Only
A two-story house with a covered porch, a brick pathway, and a large tree.
A restaurant with multiple tables set for dining, a wine bottle, and a glass of wine on the table.
A hotel room with two beds, a ceiling fan, a large window with a view of palm trees, and a painting on the wall.
A poolside area with a swimming pool, a staircase leading to a deck, and a building with multiple windows and balconies.

10. The Marquesa Hotel

The Marquesa Hotel
Old Town Key West
United States
Anna
CA $513
CA $657 total
includes taxes & fees
Oct 15 - Oct 16
The Marquesa Hotel
A modern interior with a staircase, a sofa set, a wooden table, and a television.
A pathway flanked by lush green foliage leading to a gated entrance.
A spacious room with a large bed, a sofa, a chair, a small table, and a television.
A pool area with a clear view of a house in the background, surrounded by palm trees and greenery.

11. Simonton Court Historic Inn & Cottages

Simonton Court Historic Inn & Cottages
Key West Historic District
United States
William
CA $284
CA $320 total
includes taxes & fees
Oct 14 - Oct 15
Simonton Court Historic Inn & Cottages
A pool area with lounge chairs and palm trees.
A modern outdoor seating area with a sofa, chairs, and a small table, surrounded by glass doors and a view of greenery.
A reception area with a modern design, featuring a reception desk, a sofa, and a potted plant.
A neatly made bed with patterned pillows, a bedside table with a bottle and glasses, and a window with orchids.

12. Santa Maria Suites

Santa Maria Suites
Old Town Key West
United States
Anthony
CA $427
CA $577 total
includes taxes & fees
Oct 14 - Oct 15
Santa Maria Suites
A wooden deck with white railings, surrounded by lush greenery and a staircase leading to a building.
A hallway with a white door, a wooden bench, a blue sofa, and a staircase with a white railing.
A two-story building with a white picket fence, a mailbox, and a small tree in front.
A lush garden with a variety of tropical plants and a paved walkway.

13. Duval House

Duval House
Old Town Key West
United States
Cliff
CA $250
CA $312 total
includes taxes & fees
Oct 28 - Oct 29
Duval House
A room with a bed, a ceiling fan, and a window with blinds.
A cozy outdoor seating area with a wooden bench and a table, surrounded by potted plants and a coffee and tea sign.
A poolside area with lounge chairs, a covered seating area, and a small pool.
A spacious kitchen with wooden cabinets, a granite countertop, and a ceiling fan.

14. The Mermaid & Alligator

The Mermaid & Alligator
Old Town Key West
United Kingdom
Adam
CA $366
CA $411 total
includes taxes & fees
Oct 15 - Oct 16
The Mermaid & Alligator
A narrow outdoor pathway flanked by potted plants and a wooden staircase leading to a white door with shutters.
A bedroom with a bed, nightstand, lamp, air conditioning unit, and a no smoking sign.
A two-story building with a porch, a sign reading "The Grand Guesthouse," and a purple flag.
A covered outdoor area with a wooden staircase, seating, and potted plants.

15. The Grand Guesthouse

The Grand Guesthouse
Old Town Key West
United States
Justyn
CA $210
CA $272 total
includes taxes & fees
Oct 15 - Oct 16
The Grand Guesthouse
A wooden deck with a hammock, pool, and lounge chairs overlooking a tropical garden.
A garden with a pond, rocks, and various plants.
A pool area with lounge chairs and a wooden building with balconies.
A compact kitchen with wooden cabinets, a microwave, stove, and refrigerator. There is a dining area with a table and chairs, and a sofa.

16. Island City House Hotel

Island City House Hotel
Key West Historic District
United States
Osvaldo
CA $266
CA $299 total
includes taxes & fees
Oct 15 - Oct 16
Island City House Hotel
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

17. Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
United States
sam
CA $127
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
A pool area with lounge chairs and palm trees, surrounded by boats and a sunset in the background.
A marina with boats docked, a swimming pool, and palm trees.
A hotel room with a large bed, a desk, a chair, a television, and a ceiling fan.
A balcony with a wooden table and chairs, overlooking a swimming pool and palm trees.

18. The Perry Hotel & Marina Key West

The Perry Hotel & Marina Key West
Stock Island
United States
Jade
CA $158
CA $265 total
includes taxes & fees
Oct 28 - Oct 29
The Perry Hotel & Marina Key West
A large, ornate hotel with a pool, palm trees, and a view of the ocean.
A balcony with white railings and a table, overlooking a beach with palm trees and a clear blue sky.
A grand staircase with ornate railings and a chandelier.
A large, two-story house with a prominent tower and a covered porch.

19. Southernmost House - Adult Exclusive

Southernmost House - Adult Exclusive
Old Town Key West
United States
Amy
CA $199
CA $404 total
includes taxes & fees
Oct 26 - Oct 27
Southernmost House - Adult Exclusive
A reception area with a curved marble counter, ceiling fans, large windows, and a staircase.
A bedroom with a bed, two bedside lamps, a ceiling fan, and a view of a balcony with plants.
A poolside area with lounge chairs and a clear blue pool surrounded by lush tropical vegetation.
A breakfast table with a variety of food items, including fruits, pastries, and a coffee mug.

20. Westwinds Inn

Westwinds Inn
Key West Historic District
United States
Anthony
CA $231
CA $260 total
includes taxes & fees
Oct 25 - Oct 26
Westwinds Inn
View all properties

Hotels recommended for families in Fleming Key

A pool area with lounge chairs and umbrellas, surrounded by palm trees.
A hotel room with a large bed, a wooden nightstand, a desk, a chair, and a window with curtains.
An outdoor patio area with tables and chairs, a bar area with a counter and bar stools, and a TV mounted on the wall.
A wooden outdoor dining table set with glassware, candles, and lanterns, surrounded by lush greenery.

Fairfield by Marriott Inn & Suites Key West at The Keys Collection

Fairfield by Marriott Inn & Suites Key West at The Keys Collection
New Town
CA $217
CA $285 total
includes taxes & fees
Oct 25 - Oct 26
Fairfield by Marriott Inn & Suites Key West at The Keys Collection
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a view of the ocean.
A hotel room with a large bed, a TV mounted on a wooden cabinet, and a balcony with a view of palm trees.
A modern kitchen with a marble island, wooden cabinets, and pendant lighting.
A hotel room with a balcony, a bed, a desk, and two chairs.

Hampton Inn Key West FL

Hampton Inn Key West FL
Key West
CA $241
CA $272 total
includes taxes & fees
Oct 25 - Oct 26
Hampton Inn Key West FL
A wooden boardwalk with a palm tree and lamp post, leading to a waterfront.
A pool area with lounge chairs, palm trees, and a building with a tiled roof.
A modern restaurant with a wooden counter, seating area, and large windows.
A hotel room with a desk, two beds, a TV, a ceiling fan, and a balcony with curtains.

Courtyard by Marriott Key West Waterfront

Courtyard by Marriott Key West Waterfront
Northside Resort
CA $262
CA $295 total
includes taxes & fees
Oct 26 - Oct 27
Courtyard by Marriott Key West Waterfront
A swimming pool with lounge chairs and palm trees.
Sports facility
A bar area with a wooden counter, bar stools, and a sign that reads 'So we BEATON.'
A modern living room with a sectional sofa, a small round table, and a potted plant.

Hilton Garden Inn Key West / The Keys Collection

Hilton Garden Inn Key West / The Keys Collection
New Town
CA $175
CA $237 total
includes taxes & fees
Oct 25 - Oct 26
Hilton Garden Inn Key West / The Keys Collection
A hotel with a swimming pool, balconies, and a view of the sea.
A spacious bar area with a wooden counter and green bar stools, a seating area with a sofa and chairs, and a dining area with a table set for two.
A balcony with a view of the ocean, a table, chairs, and a railing.
A beach wedding setup with white chairs, a wooden arch, and lanterns.

Hyatt Centric Key West Resort and Spa

Hyatt Centric Key West Resort and Spa
Key West Historic District
CA $344
CA $487 total
includes taxes & fees
Oct 26 - Oct 27
Hyatt Centric Key West Resort and Spa
A hotel room with a bed, a view of the beach, a hammock, and beach chairs.
A beachfront hotel with multiple colorful buildings, a pool area, and a boat dock.
A marina with boats docked, a beach resort building, and palm trees.
A beachfront restaurant with outdoor seating, a seafood sign, and a market sign.

Ibis Bay Beach Resort

Ibis Bay Beach Resort
Northside Resort
CA $159
CA $225 total
includes taxes & fees
Oct 15 - Oct 16
Ibis Bay Beach Resort
A balcony with a view of a pool area, palm trees, and outdoor seating.
A sign for Doubletree by Hilton Grand Key Resort surrounded by lush greenery and palm trees.
A hotel room with a bed, a desk, a chair, a balcony with a view, and a ceiling fan.
A large conference room with round tables, chairs, and a central carpeted area.

DoubleTree Resort by Hilton Grand Key - Key West

DoubleTree Resort by Hilton Grand Key - Key West
Key West
CA $182
CA $253 total
includes taxes & fees
Oct 27 - Oct 28
DoubleTree Resort by Hilton Grand Key - Key West
A swimming pool with water splashing, surrounded by palm trees and a building in the background.
A hotel with a pool, bicycles, and lush greenery.
A two-story yellow house with a porch, white railings, and green shutters.
The exterior of the Silver Palms Inn with a two-story structure, a green awning over the entrance, and a palm tree to the right.

Silver Palms Inn & Historic Homes

Silver Palms Inn & Historic Homes
Old Town Key West
CA $127
CA $239 total
includes taxes & fees
Oct 25 - Oct 26
Silver Palms Inn & Historic Homes
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Top Fleming Key Hotel Reviews

More cheap stays in Fleming Key

Ibis Bay Beach Resort

Ibis Bay Beach Resort

3101 N. Roosevelt Blvd Key West FL
CA $159
CA $225 total
Oct 15 - Oct 16
includes taxes & fees
Ibis Bay Beach Resort
Hampton Inn Key West FL

Hampton Inn Key West FL

3755 S Roosevelt Blvd Key West FL
CA $241
CA $272 total
Oct 25 - Oct 26
includes taxes & fees
Hampton Inn Key West FL
Southwinds Motel

Southwinds Motel

1321 Simonton Street Key West FL
CA $199
CA $272 total
Oct 14 - Oct 15
includes taxes & fees
8.6/10 Excellent! (1,385 reviews)
Southwinds Motel
Pegasus International Hotel

Pegasus International Hotel

501 Southard Street Key West FL
CA $205
CA $303 total
Oct 15 - Oct 16
includes taxes & fees
8.2/10 Very good! (1,001 reviews)
Pegasus International Hotel
Alexander Palms Court

Alexander Palms Court

715 South St Key West FL
CA $284
CA $320 total
Oct 14 - Oct 15
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
Alexander Palms Court
Tranquility Guest House

Tranquility Guest House

302 Angela st Key West FL
CA $223
CA $378 total
Oct 15 - Oct 16
includes taxes & fees
9/10 Wonderful! (35 reviews)
Tranquility Guest House

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